You’ll be reading an account of some eminent historical figure and it’ll be like…
”Dr. Max Timeonearth, born with an incurable limp, free-solo’d Mt. Krumpet by age 19, developed a number system that underpins quantum encryption, deciphered an ancient script found in Arctic cave fungi, sketched the first accurate map of a Martian lava tube using sonar echoes, wrote a fugue for eight instruments tuned to the Fibonacci sequence, discovered REM-like brain patterns in sleeping beetles, painted murals in oils he made from volcanic ash, proved a limiting case of the Riemann Hypothesis in a dream (then verified it on a blackboard made of sea glass), proposed a biomechanical model for zero-gravity childbirth, and spent his final years creating a speculative grammar for beings made of magnetic fields—only to disappear mysteriously in 1904 after walking out the back of the monstery he founded for the reification of elven telekenisis.”
Meanwhile, I’m all “traded options for 20 years, has a blog, could beat Contra on one life 3x in a row”. What’s an ego but a scab to claw at ya know?
In Flounder Mode (13 min read), Brie Wolfson profiles modern polymath Kevin Kelly. To simply call Kelly the “founder of Wired” would be like calling Jimmy Iovine a producer. Technically true, but a sin of omission. It’s an uplifting essay in the vein of “there are many ways to be while still being excellent” that can easily get lost in our mimetic feedback loops that tend to collapse the definition of excellent into trophies, commas, or fame.
While the profile is the main course, Brie’s deeply honest intro about her own path may have been even better because its angst is deeply relatable to bona-fide achievers who took illegible paths and wonder about the counterfactual.
Brie:
I started to have a sinking feeling that I had it all wrong the whole time.
I started to reflect on my own trajectory with fear that it didn’t mirror my ambition, work ethic, or deep care about the role of work in a life. Had I pointed my ambition in the wrong direction? What did I have to show for all my effort? Had I made some irreversible, unforced error with my career? How much money had I left on the table? Would the people I respected respect me back for much longer? Despite working my butt off for a decade, I had no expertise and no line of sight into where I was going. I felt immature for placing such a high value on “fun” and “bouncing around,” and full of regret about not picking a lane (or even better, a ladder). It had become hard to explain what I was good at—most importantly to myself. My sister had recently made partner at a prestigious law firm, and it seemed easier for my parents to be proud of her than of me. I couldn’t really blame them.
Kevin Kelly would say it’s good to have an “illegible” career path—it means you’re onto interesting stuff. But I wasn’t so sure anymore.
With that intro, I point you to excerpts from this terrific profile:
Accounts of people pursuing their life’s work often include phrases like “maniacal focus” or “relentless pursuit.” I hear investors say they’re looking for founders with “a chip on their shoulder.” Facebook’s iconic ‘Little Red Book’ from 2012, which still serves as a pillar for peak tech culture, features a full-page spread that says ‘Greatness and comfort rarely coexist: A recent xeet from Reid Hoffman reads, “If a founder brags about having ‘a balanced life,’ I assume they’re not serious about winning.” Jensen Huang says he wants to “torture people into greatness.” When I was on the job hunt many years ago, an investor was pitching one of his portfolio companies by saying, with a wink, that the founder would do “whatever it takes to win.” I genuinely didn’t know what he meant by that, but it sent a shudder down my spine. Once I heard a serial founder say he started his second company “out of chaos and revenge.” I heard about another prominent CEO that looks in the mirror every morning and asks himself, “Why do you suck so much?” I read a biography of Elon Musk; he seems tortured. There’s some rumor floating around about how Sam Altman was so focused on building his first startup that he only ate ramen and got scurvy. According to Altman, “I never got tested but I think (I had it). I had extreme lethargy, sore legs, and bleeding gums.”
I asked Kelly about the tradeoffs of focusing on a single thing if you want to be great (which is what I had been getting at before). “Greatness is overrated,” he said, and I perked up. “It’s a form of extremism, and it comes with extreme vices that I have no interest in. Steve Jobs was a jerk. Bob Dylan is a jerk.”
Kris: you can infer from this that Kelly places a large negative weight on being a jerk. Today, nice guys finish last feels fully internalized in our culture. I can’t tell what’s moved faster — my perception or the culture but something moved. Kelly’s view feels contrarian and old-timey.
What does Brie get from Kelly?
Compared to this, Kelly’s version of doing his life’s work seems so joyful, so buoyant. So much less … angsty. There’s no suffering or ego. It’s not about finding a hole in the market or a path to global domination. The yard stick isn’t based on net worth or shareholder value or number of users or employees. It’s based on an internal satisfaction meter, but not in a self-indulgent way. He certainly seeks resonance and wants to make an impact, but more in the way of a teacher. He breathes life into products or ideas, not out of a desire to win, but out of a desire to advance our collective thinking or action. His work and its impact unfold slowly, rather than by sheer force of will. Ideas or projects seem to tug at him, rather than reveal themselves on the other end of an internal cattle prod. His range is wide, but all his work somehow rhymes. It clearly comes very naturally for him to work this way, but it’s certainly not the norm.
“What I’m talking about is taking your interests seriously enough to have the courage to stay moving. You can give stuff away. You can abandon things. You can tolerate failure because you know that tomorrow there is more.”
Kelly’s perspective is refreshing. Maybe ambition doesn’t need to be an anxiety disorder?